Isopropenyl acetate → HCID 57308969, compound

Temperature

10 °C

A mixture of 4-(3-bromopropyloxy)-γ-oxo-β-methylbenzenebutanoic acid (50 g), anhydrous cupric sulfate (50 g), isopropenyl acetate (200 ml) and toluene (200 ml) was refluxed in an atmosphere of nitrogen for 30 minutes during which about 150 ml of the distillate was collected. The mixture was cooled, diluted with ethyl acetate (150 ml) and filtered through a bed of Celite. The solid was washed with ethyl acetate (150 ml) and the combined filtrates were washed with saturated NaHCO3 (100 ml×4), brine (100 ml×2) and dried over Na2SO4. The organic layer was concentrated and the residue was dissolved in ethyl acetate (about 300 ml). Platinum oxide (PtO2) (3.0 g) was added and the cooled (about 10° C.) mixture was hydrogenated at 20 p.s.i. H2 pressure for 90 minutes. The mixture was filtered, concentrated and the residue was purified by (suction) chromatography on silica gel to provide the title compound as an oil, uncontaminated with the (5S, 4S) and (5R, 4R) diastereomers as determined by NMR.

1. temperaturewas refluxed in an atmosphere of nitrogen for 30 minutes during which about 150 ml of the distillate
2. customwas collected
3. temperatureThe mixture was cooled
4. additiondiluted with ethyl acetate (150 ml)
5. filtrationfiltered through a bed of Celite
6. washThe solid was washed with ethyl acetate (150 ml)
7. washthe combined filtrates were washed with saturated NaHCO3 (100 ml×4), brine (100 ml×2)
8. dry with materialdried over Na2SO4
9. concentrationThe organic layer was concentrated
10. dissolutionthe residue was dissolved in ethyl acetate (about 300 ml)
11. additionPlatinum oxide (PtO2) (3.0 g) was added
12. filtrationThe mixture was filtered
13. concentrationconcentrated
14. customthe residue was purified by (suction) chromatography on silica gel

ORD record

ord-50edc7545ca64bebbbf362d3a30c9e05

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04857659